Sodium Chloride → Boc-Phe-Gly-Val-Gly-OBzl

HRID 1110691Notes

Reaction equation

HRID 1110691 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:35][CH2:36][C:37]([NH:39][C@H:40]([C:44]([NH:46][CH2:47][C:48]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:49])=[O:45])[CH:41]([CH3:43])[CH3:42])=[O:38].[Na+].[Cl-]>CN(C)C=O>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([NH:35][CH2:36][C:37]([NH:39][C@H:40]([C:44]([NH:46][CH2:47][C:48]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:49])=[O:45])[CH:41]([CH3:43])[CH3:42])=[O:38])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 131716728H-Gly-Val-Gly-OBzl

Product 1

HCID 131715249Boc-Phe-Gly-Val-Gly-OBzlYield 81.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Boc-Phe-OH (9.16 g, 34.54 mmol) was dissolved in 100 ml of dimethylformamide (DMF), cooled to 0° C. and N-methylmorpholine (NMM) (3.83 ml) added. The solution was cooled to -15° C. and isobutyl chloroformate (IBCF) (3.96 ml, 30 mmol) was added slowly under stirring while maintaining the temperature at -15°±1° C. After stirring at this temperature for 15 minutes, a precooled solution of II (9.4 g, 21.59 mmol) and NMM (2.4 ml) in DMF (40 ml) was added and stirring continued for two hours at ice-bath temperature. A saturated solution of KHCO3 was added to bring the pH to 8.0 and stirred for an additional 30 minutes. The reaction mixture was poured into a cold 90% saturated NaCl solution (1000 ml) and the precipitate obtained was filtered, washed with satd. NaCl, H2O and dried. The peptide was crystallized from ethyl acetate to give 10 g of III (yield: 81.5%). Rf2 0.83 Anal. Calcd. for C30H40N4O7 : C 63.35, H 7.09, N 9.85%. Found: C 62.96, H 7.37, N 9.86%.

Workup

  1. temperatureThe solution was cooled to -15° C.
  2. temperaturewhile maintaining the temperature at -15°±1° C
  3. stirringAfter stirring at this temperature for 15 minutes
  4. stirringstirring
  5. stirringstirred for an additional 30 minutes
  6. customthe precipitate obtained
  7. filtrationwas filtered
  8. washwashed with satd
  9. dry with materialNaCl, H2O and dried
  10. customThe peptide was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-930201cc7999415eabf5d35c0e185aa2
Source dataset
uspto-grants-1990_12
Patent number
US04976734

Reaction notes

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